he Diamond is an apt name for albums certified for 10 million + sales by the Recording Industry Association of America. The hardest substance on earth: insoluble, impervious to penetration, secure in itself. "The formation of natural diamond requires very specific conditions," Wikipedia says. The aim of this feature is to define what made Cracked Rear View, Come On Over, Boston and The Lion King soundtrack not just sales benchmarks of their respective artists' careers, but inexplicable loci at which shrewd marketing and the inscrutability of mass market taste met to produce high-quality entertainment no one breathing could escape. This column will also study why artistic peaks like Rumours, Born in the U.S.A., Thriller, Can't Slow Down, and Hysteria deserved their sales. Each entry in this series will pose the question: why should we separate art from commerce?

Since my parents didn't get cable until 1999 I never dismissed Madonna as a videos-yes-songs-meh Camille Paglia-promoted pleasure as lots of frivolous people did too long into her career. I knew her as a radio force. I first became aware of Madonna's power to confound listeners on Memorial Day, 1985: driving home from the mall with my parents, my mom and five-year-old sister starting singing "Into The Groove" when it came on the radio. I didn't sing—why should I? I was ten years old, already conscious of the fact that boys don't duet with their parents; and, at any rate, I was a boy, and boys don't sing Madonna.

Boys don't sing Madonna. A month later my parents bought Adriana a tape copy of Like A Virgin and me, um, Wham!'s Make It Big. An act of madness—my parents thought that an album with two guys as macho as George Michael and Andrew Ridgeley was more appropriate for a boy. Since we didn't have much money I was attracted to songs about money, and although we never traded notes, Adriana must have agreed. That summer "Material Girl" and "Everything She Wants" blasted from dueling boom boxes, which showed how smart we both were: who is the Material Girl if not the "you" in the Wham! song, indifferent to how hard George Michael works to get her money?

Boys don't sing Madonna. Two years later, Licensed to Ill ruled our worlds. The guys' worlds, that is. My seventh grade crush kept her cassette of True Blue in heavy rotation; the title song, she said, reminded her of what she felt for her best friend. At twelve years old, I imagined a link between "Open Your Heart" and "She's Crafty" that would become as obvious to everyone else as it was to me. My musical segregation continued long past discovering Shadoe Stevens' "American Top 40" the following year; students in a boys' Catholic high school didn't admit to loving "Like A Prayer," even though it was exactly the kind of thing that boys Catholic high school students could understand. In an increasingly mechanized hit parade its wobbly lead vocal and guitar-bass-drums arrangement were curious choices, closer to what Guns N Roses were attempting and pitched at a similar level of operatic fervor. It was the most indescribably sexy thing I'd ever heard, filthy and gross from its synth bass to the singer's decision to croon the line, "You are a muse to me" in a British accent. "Like A Prayer" was not the Incarnation; it was Pentecost, tongues of fire setting my heart aflame with imprecise longings, although when the tempest passed I was the only one left in the room. Tipper Gore was right: pop music is subversive, a terrible influence on youth. But I was still the only one in the room.

Boys still don't sing Madonna. Visit a karaoke bar. Imitate the glide from low-sung husk to full-throated belt on "Open Your Heart." You can't. I've tried, and been booed. The prom ballad "Crazy For You" is a triumph because no singer has essayed a vocal performance so indifferent to its own nakedness, to its indecision; she can't decide whether to croon or growl, sometimes, as in the "slowly now we begin to move" section, in the same bar. She's so overcome with desire that she doesn't care how embarrassing she sounds. Proms may be fantasies, but the emotions they enact aren't. If not quite Carrie and the pig blood, they're vastating experiences for those who don't belong there, whose longings threaten to destroy this most ritualistic of adolescent courtship rites. At its core, "Crazy For You" is a song about loneliness; she's dancing with the guy she loves, but he can't match her love, and they both know it. We know it when, as the song starts to fade, Madonna mutters the three-word title without affect, sounding much older than she did ten seconds ago. It's one of the most subversive moments in any Madonna song, indeed the best proof of her unwavering faith in a Catholic god, and no one's noticed it. She understands the absurdity of loving someone who keeps mum.

The only sign of intelligence shown by the Matthew Modine-Linda Fiorentino romance Vision Quest is the way in which Madonna's appearance during the crucial slow dancing scene between the lovely couple serves as a proxy for the audience. With her jelly bracelets, skirt, bad makeup, and teased hair, she's the only normal person in the room—would you rather talk to a track star and Linda Fiorentino? Since I haven't seen the film since 1994, I can't remember if "Gambler" follows "Crazy For You"; I like to remember it this way. Best described as disco-punk, Flashdance edition, it's the most aggressive track of Madonna's career, never collected despite being a Top Five hit in England (more on The Immaculate Collection's sins later). The music is keyed to her vocals—insistent, strident, hip-thrusting; she slurs the line "You're just jealous 'cuz you can't be me" like it's a shot of Rumplemints; meanwhile Animotion synths blow up her skirt. "Gambler" is the only possible response to a slow dance in which you were left as unfulfilled as you were five minutes earlier. It deserves immortality beside "Into The Groove," which itself is as much wish-fulfillment as "Crazy For You" (the Pet Shop Boys' "Domino Dancing" was the last great song about Puerto Rican boys). The only mystery: why it's the last self-written Madonna single to date. She says she got too lazy to write songs without help, which I hope is a true story.

This is why I've never forgiven Madonna for the voice and locution lessons. The transformation reminds me of that horrifying scene at the end of The Breakfast Club when Ally Sheedy is made up to look like Molly Ringwald. Lots of critics think something similar occurred when Madonna followed her eponymous debut with Like A Virgin, helmed by Nile Rodgers with all the fixin's—too calculated next to the "raw passion" of the debut. This is nonsense; it misses how Madonna conflated notions of spontaneity and calculation (one of its producers worked with Roberta Flack). Rodgers is the ideal collaborator: this was the last time he recorded a contemporary Chic record. "Like A Virgin" is practically a Chic track, what with bassist Bernard Edwards and drummer Tony Thompson on-the-one as usual. Five years earlier, Diana Ross complained that Rodgers-Edwards treated her like a session singer on the only solo studio album for which she'll be remembered; Madonna may lack Ross' poise, but she's incapable of subsuming her personality, for better or worse. A cover of Rose Royce's "Love Don't Leave Here Anymore," Like A Virgin's one outright disaster, is the sort of anonymous showtune, requiring floodlights and hand gestures, that she handled with considerable finesse ten years later, when the inevitability of the gesture mitigated its ghastliness. Chalk it up as a sop to the detractors who think she was Eva Peron.

Fans keep The Immaculate Collection around the house because of its peerless sequencing and punchy remastering; but as a compilation it's a botch. The remixed versions of "Like a Prayer" and "Express Yourself" aren't even the best ones extant. More importantly, Madonna had had so many Top Tens in so few years that TIC actually ignores several essential to understanding her complete mastery of the pop single as a medium for self-expression and conduit for our emotions. Like A Virgin's Top Five absentees "Dress You Up" and "Angel" do a better job than the two big singles of delineating the boundaries of Madonna's determined shallowness, an act that confounds Philistines today and made the appreciation of her musical skills a lot harder than it took these critics to dismiss Cyndi Lauper as the real charlatan. "Angel" is a particular stunner, certainly the apex of Rodgers' post-Chic skills. Note the ear-catching opening: pizzicato Rodgers guitar, canned Madonna laughter, doomy keyboard; it's surprisingly moody for so giddy a lyric, until Maddie dips in and out of her lower register, only to explode in the "I can see it in your e-e-e-eyye-e-s" lyric that she no doubt lifted from PiL's "Death Disco"—a title whose implications, by the way, Madonna understood better than any disco practitioner in history (1992's Erotica could have been titled Death Disco).

Lots of men admit to singing along to Madonna now. They were boys when "Live To Tell" hit Number One in early 1986. Despite many later triumphs, this set of lyrics remain her best, matched by co-writer Patrick Leonard's sophisticated chord changes (relisten to the "If I ran away, I wouldn't have the strength to go very far" bit) and a vocal that seethes with a lifetime's worth of hurts which she nevertheless refuses to share. Still, who doubted in 1986 that she wouldn't live to tell—that she would live long enough to sing it onstage while strapped to a giant cross? We're all older, and more ridiculous, haunted by memories of proms past.